This pairing of a dark brown plaid blazer and charcoal dress pants is a never-failing option when you need to look like a true connoisseur of men's style. Burgundy leather work boots will give a more casual vibe to an otherwise dressy ensemble. When leaves change color and autumn is at its best, you'll appreciate how great this outfit is for awkward fall weather. As you can see here, as a 50-something gent, you still have a wide range of outfit options.